1. Field of the Invention
The present invention relates to the preparation of chloroacetyl chloride. More particularly, the invention relates to the preparation of chloroacetyl chloride by reacting glycolic acid with thionyl chloride in the presence of nitrogen-containing organic compound or phosphine compound.
2. Description of the Prior Art
Comptes Rendus, Volume 152, page 1601, dated June 6, 1911, shows the preparation of alkyl chloride by the reaction of alcohol and thionyl chloride in the presence of a molar amount of pyridine as acid acceptor.
Comptes Rendus, Volume 174, page 1173, dated May 1, 1922, shows the production of chloroacetyl glycolyl chloride by reaction of glycolic acid and thionyl chloride.
Survey of Organic Synthesis by Buehler and Pearson, pages 860 and 861, published 1970 by Wiley-Interscience, New York, shows the production of acyl chlorides by reaction of the acid and thionyl chloride employed with iodine or with a trace of pyridine.
U.S. Pat. No. 2,848,491 shows the preparation of carboxylic acid chlorides by reaction of the acid with phosgene in the presence of nitrogen-containing compounds and mentions the preparation of chloroacetyl chloride from chloroacetic acid.
U.S. Pat. No. 3,418,365 shows the preparation of beta-chloropropionyl chloride by the reaction of beta-propiolactone with thionyl chloride.
U.S. Pat. No. 3,758,659 shows the preparation of chloroacetyl chloride by reaction of ketene with chlorine in the presence of alpha-butyl-gamma-butyrolactone.
U.S. Pat. No. 3,880,923 shows the preparation of mono-chloroacetyl chloride by reaction of acetyl chloride and chlorine in sulfuric acid.
U.S. Pat. No. 3,883,589 shows the preparation of chloroacetyl chloride by reaction of ketene and chlorine in the presence of a tertiary phosphate ester such as tris(2-chloroethyl) phosphate.